Glyoxal → delta-Gluconolactone

Participants

Reaction Steps

2-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)acetimidohydrazide (compound 45, crude 1 g from step 1) in EtOH (30 ml) reacted with glyoxal (5 ml, 30% in water) at 0° C., and allowed to warm up at room temperature. After the reaction mixture was stirred for 3 hours, it was evaporated under reduced pressure to remove volatile compounds. The residue was purified with silica gel (Hx/EtOAc=⅓) to provided title compound (324 mg, 60% overall yield form intermediate 2).

Provenance & Evidence